Literature DB >> 29135249

Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism.

Aleksandar R Todorov1, Tom Wirtanen1, Juho Helaja1.   

Abstract

Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G** level can predict the reactivities of the studied substrates.

Entities:  

Year:  2017        PMID： 29135249     DOI： 10.1021/acs.joc.7b02775

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study.

Authors:  Julien Pedron; Clotilde Boudot; Sébastien Hutter; Sandra Bourgeade-Delmas; Jean-Luc Stigliani; Alix Sournia-Saquet; Alain Moreau; Elisa Boutet-Robinet; Lucie Paloque; Emmanuelle Mothes; Michèle Laget; Laure Vendier; Geneviève Pratviel; Susan Wyllie; Alan Fairlamb; Nadine Azas; Bertrand Courtioux; Alexis Valentin; Pierre Verhaeghe
Journal:  Eur J Med Chem       Date:  2018-06-05       Impact factor: 6.514

2.  S,S-Chiral Linker Induced U Shape with a Syn-facial Sensitizer and Photocleavable Ethene Group.

Authors:  Goutam Ghosh; Sarah J Belh; Callistus Chiemezie; Niluksha Walalawela; Ashwini A Ghogare; Mariana Vignoni; Andrés H Thomas; Sherri A McFarland; Edyta M Greer; Alexander Greer
Journal:  Photochem Photobiol       Date:  2018-09-27       Impact factor: 3.421

Review 3.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

4.  Design, synthesis and biological evaluations of a long-acting, hypoxia-activated prodrug of fasudil, a ROCK inhibitor, to reduce its systemic side-effects.

Authors:  Taslim A Al-Hilal; Mohammad Anwar Hossain; Ahmed Alobaida; Farzana Alam; Ali Keshavarz; Eva Nozik-Grayck; Kurt R Stenmark; Nadezhda A German; Fakhrul Ahsan
Journal:  J Control Release       Date:  2021-04-26       Impact factor: 11.467

5.  Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant.

Authors:  Aleksandar R Todorov; Santeri Aikonen; Mikko Muuronen; Juho Helaja
Journal:  Org Lett       Date:  2019-05-08       Impact factor: 6.005

6.  Synthesis of N-Bridged Pyrido[4,3-d]pyrimidines and Self-Assembly into Twin Rosette Cages and Nanotubes in Organic Media.

Authors:  Cansu Igci; Osman Karaman; Yiwen Fan; Arthur A Gonzales; Hicham Fenniri; Gorkem Gunbas
Journal:  Sci Rep       Date:  2018-10-29       Impact factor: 4.379
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.